14U Headless Horseman
14U Headless Horseman is a youth travel softball tournament in New Windsor, NY, held Sat, Sep 12 – Sun, Sep 13, 2026. Age groups: 14U. Part of the USSSA Fastpitch calendar.
This tournament has finished. Here is what is on nearby next: softball tournaments in New York in the next 30 days.
From the organizer's listing on usssa.com · checked Oct 19, 2026.
Age groups and entry fees
| Division | Teams registered | Entry fee |
|---|---|---|
| 14U Open | 8 | $578 |
How strong is the field?
- 14U: Balanced field. 8 teams registered, 8 with results we can rate. Strongest entered: NJ Vipers White, Northeast Devils 14u Castro and Top Level Athletics 13U.
Ratings come from public game results. How field ratings work. The 1-10 rating for each field and every registered team are in the TourneyMagic search.
Last year
14U Headless Horseman Classic ran Sat, Sep 27 – Sun, Sep 28, 2025 in New Windsor, NY. 16 teams entered in 14U. The 14U field was rated a strong field.
Other softball tournaments near New Windsor that weekend
- Fall Extravaganza · Chester, NY · 15 mi · 10U, 12U, 14U, 18U · 27 teams
- Dust off the Rust - LIN · Linden, NJ · 60 mi · 14U · 10 teams
- Home Runs for Heroes · Hauppauge, NY · 62 mi · 12U, 14U, 16U, 18U · 38 teams
- Play for Rhiannon · Hauppauge, NY · 62 mi · 14U, 16U, 18U · 14 teams
- NEVER FORGET 3rd Ann · Hauppauge, NY · 62 mi · 12U, 14U, 16U · 15 teams
- Bases Loaded Fastpitch Fall League · Yaphank, NY · 73 mi · 8U, 10U, 12U, 14U, 16U · 4 teams
Every softball tournament in New York that weekend, with field ratings
New York softball tournaments · Softball tournaments by region
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Page updated Oct 19, 2026.